She Climbed from Marketing Manager to CMO, Then Walked Away. Here’s Why.
How Annie Katrina Lee reframed success and reimagined her career
Hey 👋 I’m Andrew. Welcome to Delivering Value - the newsletter and podcast where I interview SaaS leaders about the toughest moments of their careers, and explore how they turned them into success stories. Learn from their mistakes, without the pain.
The Dream Job That Wasn’t
Annie Katrina Lee has the career story most marketers dream about.
She landed her first big break at Microsoft after handing her resume to a guest speaker at a college event. That gutsy move led to an interview and, ultimately, her first job in marketing, working on Bing.
She went on to become the first marketing hire at Pinterest, worked at Amazon, was on the Senior Leadership team at Twitch, and became CMO at Brave.
She had the title every marketer wants.
But inside? Something felt off. She felt incomplete.
"I kind of lost my love for the craft," she told me. The excitement and problem-solving that once fueled her was buried under layers of meetings and executive politics. She would wake up questioning whether the work she once loved still had a place in her life.
This is the story of how Annie went from an ambitious marketing manager to a CMO - and why she walked away when she got there.
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Small-Town Ambition Meets Big-Tech Reality
Annie grew up between two wildly different places - Augusta, Georgia, and the Big Island of Hawaii.
In high school, she set a goal to be in nearly every club. “Which was really silly because that's just a recipe for spreading yourself thin,” she laughed.
When she got to college, she wrestled with what she wanted to do. She changed majors multiple times - starting in fine arts, then communications, then finance, before finally settling on marketing.
“It was the perfect balance of storytelling, analytics, and human psychology,” she said.
One day, a guest speaker from Microsoft spoke in one of her classes, and she boldly handed him her resume. “I didn’t think anything of it,” she said.
“Like, I would be very lucky if I got a call back.”
Annie did get a call back. And that gutsy move landed her an interview that started her career in search marketing at Microsoft, working on (what would eventually become) Bing.
From there, her career took off.
The High-Stakes Climb - and the Hidden Cost
It took 16 years for Annie to climb the marketing totem pole.
Microsoft. Amazon. Pinterest. Twitch. Each move was a step up. Each move gave her more influence, more impact, more responsibility, and more money.
In 2022, Annie accepted a role as CMO.
She had everything she thought she wanted.
But something felt… off.
She was exhausted. Work was consuming her. She had a young daughter at home that she wanted to spend more time with. And for the first time, she started to question the path she had been climbing for years.
“I got a peek behind the curtain of the executive world, and it just didn’t feel right,” she said. “I felt like I had lost my love for the craft.”
Had she outgrown the role, or had the work changed in a way that no longer felt fulfilling? Was she chasing a vision of success that no longer aligned with what she truly wanted?
The Moment of Clarity That Changed Everything
When I interview guests for my show, they’ll usually share a single moment that pushed them, to cannonball from their old life, into something new
For Annie, it was waiting in the car pickup line at her daughter’s school.
She saw her daughter’s face light up when she pulled in.
“That moment made me realize there’s an expiration date for this window of magical childhood where she looks at me like I'm the best thing since sliced bread. This won’t last forever. I want to relish it and soak it up as much as possible. My career will always be there. But this? This time with her? This has an expiration date.”
And that was the moment she decided to step away from the CMO track.
The Aftermath: Walking Away from the Dream
“People thought I was crazy,” Annie said.
“They said, ‘You can’t leave now! You’ve worked so hard to get here!’ But I just knew in my gut that it was not the right fit or not the right moment”
She walked away. Left the CMO title behind. And took a different path.
Today, Annie is a fractional CMO, an advisor, and the co-founder of Penknife Collective where she gets to apply her skills in new ways, on her own terms.
She didn’t lose her love for the craft.
She still loves marketing “I still geek out over it all the time,” she shared. But she does it in a way that aligns with her life, not at the expense of it.
What Can We Take Away from Her Story?
Annie’s story is a reminder for any leader at a crossroads:
Success doesn’t always feel like success. Getting the title, the salary, the status - it doesn’t mean you’ll feel fulfilled when you get there.
Loving your craft doesn’t mean loving every job. Annie thought she had fallen out of love with marketing. But really, she had fallen out of love with how she was doing it.
There’s no shame in leaning out. “We’ve spent years being told to lean in, but sometimes, you need to lean out,” Annie said. And that’s okay.
The window of time with people we love is short. Work will always be there. Your career will always be there. But some moments: picking up your kid from school, having dinner with your family, spending time with a grandparent - have an expiration date.
Your career is yours to design. Just because the traditional path says you have to keep climbing doesn’t mean you have to follow it. You can step sideways. You can step back. You can redefine success on your own terms.
Annie isn’t saying you shouldn’t work hard to climb the corporate ladder. But she is challenging you to redefine success on your own terms.
Are you climbing simply because it’s what’s expected, or are you creating a career that aligns with your values and priorities?
Annie’s story is a masterclass in redefining success. Too often, we chase titles and prestige, only to realize they come with a hidden cost... our time, energy, and even our love for the craft. The fact that she walked away at the ‘peak’ says everything about what real success looks like: designing a life, not just a career. Great article, Andrew.